Synthesis and Biological Properties of Gemini Quaternary Ammonium Compounds, 5,5'-[2,2'-(α,ω-Polymethylnedicarbonyldioxy)diethyl]bis-(3-alkyl-4-methylthiazolium iodide) and 5,5'-[2,2'-(p-Phenylenedicarbonyldioxy)diethyl]bis(3-alkyl-4-methylthiazolium brom
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概要
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We synthesized gemini quaternary ammonium compounds (gemini QACs) having two thiazolium moieties in a molecule, 5,5'-[2,2'-(α,ω-polymethylnedicarbonyldioxy)diethyl]bis(3-alkyl-4-methylthiazolium iodide) (5DEBT-m,n), on which the carbon number of the methylene chain linking the two thiazoles (m) is 2, 6 or 8 and that of the alkyl group (n) is 8, 10, 12, 14 or 16. 5,5'-[2,2'-(p-Phenylenedicarbonyldioxy)diethyl]bis(3-alkyl-4-methylthiazolium bromide) (5DEBT-P,n) was then synthesized, which is composed of a p-phenylene as the methylene spacer. For five gemini QAC series, in addition to the previously described 5DEBT-4,n to the four new compound series, their antimicrobial activities were determined. 5DEBT-m,10 and -P,10 exhibited a wide and strong bacteriostatic activity against gram-negative and -positive bacteria, fungi and then yeast in comparison with N-tetradecyl-5-(2-hydroxyethyl)-4-methylthiazolium iodide as a mono-QAC. The bactericidal activity of the 5DEBT series against Escherichia coli IFO 12713 and Staphylococcus aureus IFO 12732 was investigated on the basis of the effects of their alkyl chain length and their molecular hydrophobicity. It was found that the effect of theses factors on their activity significantly changes by the difference between the gram-negative and -positive bacteria. Although against the gram-negative bacterium, the change in the activity due to extension of the alkyl group for each compound affected the kind of methylene spacer, against the gram-positive bacterium, it was almost equal in spite of the methylene spacer. This result could be responsible for the bactericidal mechanism of the gemini QACs being influenced by the diversity of the steric structure participating in the methylene chain length and by the bacterium cell surface hydrophobicity.
- 公益社団法人日本薬学会の論文
- 2006-05-01
著者
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Takagi Mutsumi
Pharmaceutical Research And Development Department Asahi Chemical Industry Company Ltd.:(present Add
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MAEDA Takuya
Department of Tropical Medicine and Parasitology, School of Medicine, Keio University
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Maeda Takuya
Department Of Biotechnology Faculty Of Eigineering Osaka University
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Maeda Takuya
Department Of Biological Science And Technology Faculty Of Engineering The University Of Tokushima
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Yoshida Munehiro
Takamatsu Works Inui Corporation
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Takagi M
Japan Advanced Inst. Sci. And Technol. Ishikawa Jpn
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Yoshida M
Takamatsu Works Inui Corporation
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SHIRAI Akihiro
Department of Biological Science and Technology, Faculty of Engineering, The University of Tokushima
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SUMITOMO Tomoko
Department of Biological Science and Technology, Faculty of Engineering, The University of Tokushima
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KAIMURA Tomoyo
Department of Biological Science and Technology, Faculty of Engineering, The University of Tokushima
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NAGAMUNE Hideaki
Department of Biological Science and Technology, Faculty of Engineering, The University of Tokushima
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KOURAI Hiroki
Department of Biological Science and Technology, Faculty of Engineering, The University of Tokushima
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Kourai H
Department Of Biological Science And Technology Biosystems Engineering Institute Of Technology And S
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Kourai Hiroki
Department Of Biological Science And Technology Faculty Of Engineering The University Of Tokushima
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Kaimura Tomoyo
Department Of Biological Science And Technology Faculty Of Engineering The University Of Tokushima
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Sumitomo Tomoko
Department Of Biological Science And Technology Biosystems Engineering Institute Of Technology And S
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Shirai Akihiro
Department Of Biological Science And Technology Biosystems Engineering Institute Of Technology And S
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Maeda T
Laboratory Of Biochemistry And Molecular Biology Graduate School Of Pharmaceutical Sciences Osaka Un
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Nagamune Hideaki
Department Of Biological Science And Technology Faculty Of Engineering The University Of Tokushima
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Maeda Takuya
Department of Agricultural Chemistry, University of Osaka Prefecture
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Kourai Hiroki
Department of Applied Chemistry, Technical College of Tokushima University
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